Incredibly Weird and Sexual Oneshots
by HSMFan2006
Summary: A weird (but fun) oneshot with Troy and someone unexpected. First ever fanfiction with these 2 reacting like this (from what I could find, anyway). This has seemed to turn into more than I expected; I'm glad, though.
1. Troy Bolton and Maria Montez

**I've had this twisted idea floating in my head for a while... and considering I've never seen anything like this before, I figured I might as well be the first. I know, the idea is incredibly bizzare but I tried to make it work. I guess if someone wanted more, I wouldn't be against doing another chapter, since the ending leaves open for more. I'd need some suggestions though. Considering this is the first sexual Fanfiction I've ever done, I'd say it came out good enough. I suppose this takes place inbetween HSM1 and HSM2. I gotta admit, writing this was actually a fun , enjoy!**

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Maria Montez's (Gabriella's mother) POV

It seemed to happen every Thursday, now that Troy and Gabriella were dating; Troy hung out here afterschool, in Gabi's room, waiting for her to get home from afterschool Decathlon club. I have to admit, I've always been somewhat curious as to what Troy does in Gabriella's room while he waits for her to come home. I mean, there's an entire hour between him and her getting here. Would a little peek hurt? No. No, I can't, its his business, not mine. Suddenly, I heard a groan from Gabriella's room. A groan? Was Troy hurt? I rushed upstairs to Gabriella's room and opened the door.

"Troy, are you alr-"

I opened the door to find Troy on Gabriella's bed, naked from the waist down, stroking himself. He noticed me, and quickly fell off Gabriella's bed. I could easily tell how freaked out he was. Honestly, I could sympthise with him a little; the boy needed to release, and it obviously wasn't happening easily for him. He suddenly spoke very quickly, almost as if his life depended on it.

"Mrs. Montez, listen, I'm so sorry, I mean I-"

"Troy, don't worry about it, I get it. Not the worst thing I could've walked in on."

 _I have to admit, the boy did have a nice erection._

Wait, no, this is Gabriella's boyfriend, I certainly can't think like that, can I?

 _You can think anything you want, its not like he can hear you._

I then realized I had been standing there silently for about 20 seconds, staring directly at the erection in his boxers.

"Uhhh, Mrs. Montez?"

"Oh, sorry Troy."

More silence; I couldn't stop staring at his erect cock; I'd be surprised if Gabriella hadn't already seen it. Then again, they are both responsible teenagers.

"Troy, can I ask you something?"

"Um, sure?"

It sounded more like a question on his end, but I continued anyway.

"Have you and Gabriella done anything... sexual?" He looked down at the bed he was sitting on, and turned a light shade of pink in the face.

"Uh, no.. but we don't wanna rush into anything crazy."

Should I offer him help?

 _Do it! It's been so long since we've seen any action!_

He looked incredibly uncomfortable, so I figured now would be the best time to spit it out.

"Troy, I'm willing to help you, this one time."

"What?"

I scooted a little closer, and put my hand on his erection, which was still covered by his boxers. He groaned at the sudden contact.

"I'm willing to help you... release. Just this one time though. And of course, it would have to stay between us."

He looked dumbfounded, I can tell he didn't expect me to say that.

"Seriously? You wouldn't tell Gabriella?"

I winked. "Gabriella isn't gonna help you yet, and somone clearly has to." I got down on my knees in front of Troy, and pulled off his boxers, revealing his full cock to me. I gasped; this thing was **huge**! I unbuttoned the top 3 buttons on my shirt (a little cleavage for his eyes wouldn't hurt, right?), and then I began to slowly stroke his cock, earning a moan from Troy.

"Mmmm, Mrs. Montez.."

"Call me Maria", I said seductively.

He put his hand through my hair as I began stroking his cock slightly faster. He groaned softly as I sped up my actions, unknowingly notifying me that I was doing a good job. Then, I had a interesting thought; if his cock felt this good in my hands, would it feel even better in my mouth?

 _Go for it, you've already gotten this far on taking chances!_

I stopped stroking his cock, to which he removed his hsnd from my hair and looked down at me, confused. I then took off my shirt entirely, followed by my bra, giving him full view of my D Cup tits. While he was staring at them, I licked his tip, making him shudder in ecstasy.

"You like that, big boy?"

"Oh god, I love it Maria.."

I then began to slowly insert his cock into my mouth, trying not to gag on it. I then swirled my tongue around the tip, making him moan my name loudly. He then put his hand back in my hair, and began pushing my head up and dpwn, making me gag slightly, but then we found a rhythm and he was loving it. He looked down at me, and I winked once again. Suddenly his cock twitched, and I knew what was coming.

"Can... cum.. tits?"

He couldn't even form full sentences right now, but I mnew what he wanted; he wanted to cum on my breasts. Should I let him?

 _Do it, you know you want it!_

I then pulled him out of my mouth, and began to once again stroke him, getting no response, other than heavy panting and loud moans.

"Come on sexy, cum all over my tits!"

"..I'm cumming, Maria!"

He suddenly sprayed his load all over my tits, watching his cock twitch the entire time. When he was finally done, he layed back on the bed, and I took a chance.

I kissed him; a kiss he moaned into.

I got out of the kiss, grabbed my bra and shirt, and walked towards the bathroom, as it was obvious we both needed to clean up.

"Oh, and Troy?"

"...Yeah?"

"Remember when I said we'd only do this once?"

He nodded, still panting.

"If you ever need more help, come find me, I'll help you as many times as Gabriella won't."

I winked one final time, and then walked out of Gabriella's bedroom, leaving the young boy inside pleased, confused, and flabbergasted.

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 **Weird, right? It's good enough, I suppose. If you want another one of these, leave a review, I'd be up for more of these, actually.**


	2. Troy Bolton and Maria Montez 2

**People wanted yet another one of these, and I'm more than happy to give it to you... totally up for making a third one, if its wanted. My only issue with the last one was its short length; I'll try to remedy that here. I think I should tell you that the italics is basically Maria's deepest thoughts, her sexual side, if you will. This takes place after Gabriella and Troy kiss in HSM2, but before they stopped working at Lava Springs. Enjoy!**

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Maria Montez's (Gabriella's mother) POV

It was Summer; all the kids, including Gabriella, were out having fun, or working. While I was stuck home, alone, bored. But at least Gabriella was out, probably with her friends. I really need some new friends in the area, I know so very few here...

 _You know Troy Bolton._

Of course I do, he's dating Gabriella, he's a wonderful young man.

 _I don't mean on that level, you know that._

That meant nothing to me, you and I are both aware of that.

 _Sure it didn't.. and you also didn't enjoy blowing him; admit it, you want him in more ways than one._

Alright, so maybe I do, but what am I supposed to do about it?

 _Isn't he coming over soon to pick up Gabriella for work?_

Yeah, but Gabriella left early today.

 _Exactly, it'll just be him and you._

And exactly what am I supposed to do?

 _I don't know, seduce him, kiss him, ANYTHING! Just come up with some sort of plan to get him wanting you._

 **Knock, knock, knock!**

I looked out the window, and it was none other than Troy.

 _Showtime!_

I opened the door, shirt unbuttoned at the top, to a somewhat confused teenager with blue eyes.

"Mrs. Montez?"

"Oh, hello Troy! Please, come in!"

The boy walked in, looking around as if the house was foreign to him.

"Uh, is Gabriella here? I'm supposed to walk with her to work at Lava Springs."

"I'm sorry Troy, she left early this morning... but, I'm here."

"What?"

I kissed him harshly and quickly on the lips, which shocked him quite a bit. He somewhat quickly pulled away from my lips, much to my dismay.

"Mrs. Montez, what are yo-"

I put my hand on his crotch, earning a slight groan from him. Wow, this kid was incredibly sensitive down there.

"Sweetheart, what did I tell you? You can call me Maria."

"Wait, we're doing this again?"

"Troy... I need you."

He looked shocked; I knew this was the first time someone had said this to him sexually.

"Wait, are you serious?"

I kissed him again, this time passionately. He quickly stuck his tongue in my mouth, which in turn, made me moan. We did this until we had to separate for air. I then pulled off my shirt, and unclippsed my bra. He simply stared at my naked breasts, seemingly unsure on what to do.

"Troy, you can touch them, you know. You can do whatever you want. I'm your sex canvas."

He slowly moved his hands toward my breasts, but I stopped him.

"You can do whatever you want, on a condition."

"What is it?"

"Take off your clothes."

"Wait, that's it?"

"That's it, Troy."

He quickly stripped himself of his shirt, pants, and boxers. The boy was already erect, and he had gotten even bigger.

"Wow, you've gotten even bigger, Troy!"

"Um, thanks, I think."

He quickly grabbed my breasts and squeezed them, causing me to moan his beautiful name loudly.

"You know, you kiss even better than Gabriella."

"Do I really?"

"Wait, lemme make sure..."

He pulled me in for a kiss again, a long one.

"Yeah, your much better than Gabriella."

I grabbed his cock and stroked it, making us both fall onto the couch in the living room.

"You like that, sexy? You like it when I stroke your cock?"

He response was to suck on my left nipple, causing me to almost scream in pleasure.

"Well, I can tell you like that.. I wonder how the right one tastes.."

He then sucked on my right breast, licking my nipple, swirling over it with his amazing tongue.

"Oh god, Troy, you're amazing!"

"If you think I'm amazing now, wait until I do this.."

He stuck his pointer and index finger into my pussy, causing me to scream his name in ecstasy.

"Maria, your so wet!"

"All for you, baby..."

"I'd love to stick my dick in there."

"Do it, Troy! Fuck me hard!"

"I don't have a condom on me..."

"I don't care, I need your dick inside me!"

"Get on your hands and knees, Maria."

I followed his command, and he slowly shoved his long dick into my wet pussy, both of us moaning at the contact. He started slow, but then he cupped my breasts and sped up his actions, and we found a rhythm together. The sounds of pants and moans filled the room, until I spoke.

"Troy, I'm cumming!"

I came with him inside, and my orgasm set off his, my pussy now filled with his cum.

We layed side by side, panting, before he spoke.

"That was my first time."

"Well Troy, it didn't show."

Silence filled the air, so I slowly stood up and grabbed my clothes, about to leave the room so he could clean himself up.

"Troy, you know we're gonna end up doing this again, right?"

"I was hoping you'd say that."

"Good, because you and your cock work amazing together."

I then left the room, swaying my sweat covered hips.

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 **I suppose the question is now, where do I go from here? I really want to do more with these characters.. more suggestions would be great!**


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